Chin. J. Org. Chem. ›› 2006, Vol. 26 ›› Issue (12): 1667-1672. Previous Articles     Next Articles

Original Articles

中国南海裸鳃目软体动物美丽拟皮片鳃(Dermatobranchus orna-tus)及其可能的食源动物柳珊瑚Muricella sp.的化学成分研究

张文a,GAVAGNIN, Margheritab,郭跃伟*,a,MOLLO, Ernestob
CIMINO, Guidob   

  1. (a中国科学院上海生命科学研究院药物研究所国家新药研究重点实验室 上海 201203)
    (b Istituto di Chimica Biomolecolare-CNR, I-80078 Napoli, Italy)
  • 收稿日期:2006-03-21 修回日期:2006-06-02 发布日期:2006-11-21
  • 通讯作者: 郭跃伟

Chemical Studies on the South China Sea Nudibranch Dermato-bran- chus ornatus and Its Suggested Prey Gorgonian Muricella sp.

ZHANG Wena,GAVAGNIN Margheritab,GUO Yue-Wei*,a,MOLLO Ernestob
CIMINO Guidob   

  1. (a State Key Laboratory of Drug Research, Institute of Materia Medica, Shanghai In-stitute for Biological Sciences,
    Chinese Academy of Sciences, Shanghai 201203, China)
    (b Istituto di Chimica Biomolecolare-CNR, I-80078 Napoli, Italy)
  • Received:2006-03-21 Revised:2006-06-02 Published:2006-11-21
  • Contact: GUO Yue-Wei

Four diterpenoids with eunicellane carbon skeleton, namely ophirin (1), calicophirin B (2), 13-deacetoxyl calicophirin B (3) and 13-deacetoxyl-3-deacetyl calicophirin B (4), were isolated from the South China Sea nudibranch Dermatobranchus ornatus, whereas calicophirin B (2), 13-deacetoxyl calicophirin B (3), astrogorgin (5) and an unnamed analogue 6 were obtained from gorgonian Muricella sp., simultaneously collected from the same region as that of D. ornatus. Structures of these compounds 16 were elucidated on the basis of detailed spectroscopic analysis and by comparison with those reported data, and a complete 1H and 13C NMR assignment of ophirin (1) was carried out for the first time. An X-ray diffraction analysis on a single crystal of ophirin (1) not only confirmed the established structure but also led to a revised stereochemical illustration for the above metabolites. This is the first report of chemical studies on the nudibranch of genus Dermatobranchus, which suggests that Dermatobranchus ornatus can protect themselves from predators by selecting appropriate diet, and consequently transforming and bio-accumulating some useful dietary metabolites into selected body parts as defensive substances. The discovery of similar compounds from both the molluscs and the gorgonian suggests a probable predator and prey relationship between them.

Key words: Dermatobranchus ornatus, nudibranchia, gorgonian, eunicellane diterpenoid, Muricella sp.